Issa Rae and the growing pains of being ‘Insecure’

Five years after the debut of “Insecure,” the acclaimed HBO comedy-drama is finally coming to a close. Creator and star Issa Rae discusses the characters’ journeys, personal growth and “betting on herself.”

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For a certain generation of Black women, Issa Rae’s volume of work is like the Harry Potter books — stories about characters who grow and mature alongside their fans.

“In shooting this final season, we've been very nostalgic and thinking about where we came from and imagining what our impact would be like,” says Rae, the creator and star of HBO’s “Insecure.” “Maybe people will hold on to this show as part of their lives in that way, and we may go down in history, you know, if we stick the landing. … And that makes me feel really good.”

“Insecure” debuted on HBO in 2016, focusing on the lives of two late-20s best friends in Los Angeles who are trying to navigate messy romances, social lives and professional aspirations. But Rae has been the voice of millennial Black women for more than a decade, all the way back to her hit Web series “The Misadventures of Awkward Black Girl.”

“I used to binge-watch this show in my dorm cafeteria on Fridays,” says Martine Powers, “Post Reports” host. “I'd be like, ‘Oh, all my essays are done, getting ready for the weekend. I'm going to watch “Awkward Black Girl.” This is going to be amazing.’”

As Rae reflects on the final season of her show, her characters’ trajectory, and her own personal growth, she says that she’s learned to trust the choices she’s made along the way that have led to greater artistic freedom — and power. 

“One of the scariest things to me … is just, like, the fork-in-the-road choice,” Rae says. “There's something so terrifying about knowing that this is a decision that I could make that could change the course of my life. And I just have to make it.”